Synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines

被引:16
作者
Agami, C [1 ]
Dechoux, L [1 ]
Ménard, C [1 ]
Hebbe, S [1 ]
机构
[1] Univ Paris 06, UMR 7611, CNRS, Lab Synth Asymetr, F-75005 Paris, France
关键词
D O I
10.1021/jo025955+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines 4 is described. The key step of the synthesis involves the stereoselective reduction of chiral nonracemic lactams 2 by using (BH3Me2S)-Me-.. A rationalization of the stereoselectivity is presented.
引用
收藏
页码:7573 / 7576
页数:4
相关论文
共 32 条
[1]   Asymmetric synthesis of nitrogen heterocycles by reaction of chiral β-enaminocarbonyl substrates with acrylate derivatives [J].
Agami, C ;
Dechoux, L ;
Hebbe, S .
TETRAHEDRON LETTERS, 2002, 43 (14) :2521-2523
[2]   NEUROMEDIATOR ANALOGS - SYNTHESIS OF CIS (2R,3S) AND TRANS (2S,3S)-2,3-PIPERIDINE DICARBOXYLIC-ACIDS FROM (2S)-2-PHENYLGLYCINOL [J].
AGAMI, C ;
KADOURIPUCHOT, C ;
LEGUEN, V ;
VAISSERMANN, J .
TETRAHEDRON LETTERS, 1995, 36 (10) :1657-1660
[3]  
Amat M, 2002, ANGEW CHEM INT EDIT, V41, P335, DOI 10.1002/1521-3773(20020118)41:2<335::AID-ANIE335>3.0.CO
[4]  
2-Y
[5]   Resolution of delta-lactams provides access to nonracemic benzoquinolinones: The synthesis of LY300502 and LY300503 [J].
Astleford, BA ;
Audia, JE ;
Deeter, J ;
Heath, PC ;
Janisse, SK ;
Kress, TJ ;
Wepsiec, JP ;
Weigel, LO .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4450-4454
[6]   A diastereoselective tandem metalloenamine alkylation/aza-annulation of beta-tetralones expedites the synthesis of benzoquinolinones [J].
Audia, JE ;
Droste, JJ ;
Dunigan, JM ;
Bowers, J ;
Heath, PC ;
Holme, DW ;
Eifert, JH ;
Kay, HA ;
Miller, RD ;
Olivares, JM ;
Rainey, TF ;
Weigel, LO .
TETRAHEDRON LETTERS, 1996, 37 (24) :4121-4124
[7]   Formation of dihydropyridone- and pyridone-based peptide analogs through aza-annulation of beta-enamino ester and amide substrates with alpha-amido acrylate derivatives [J].
Beholz, LG ;
Benovsky, P ;
Ward, DL ;
Barta, NS ;
Stille, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :1033-1042
[8]   Aza-annulation as a versatile approach to the synthesis of non-benzodiazepene compounds for the treatment of sleep disorders [J].
Benovsky, P ;
Stille, JR .
TETRAHEDRON LETTERS, 1997, 38 (49) :8475-8478
[9]   Asymmetric formation of quaternary centers through aza-annulation of chiral β-enamino amides with acrylate derivatives [J].
Benovsky, P ;
Stephenson, GA ;
Stille, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) :2493-2500
[10]   Enantioselective synthesis of ethyl nipecotinate using cinchona modified heterogeneous catalysts [J].
Blaser, HU ;
Honig, H ;
Studer, M ;
Wedemeyer-Exl, C .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 139 (2-3) :253-257